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Synthesis, characterization, and NMR studies of 1,2,3-triazolium ionic liquids: a good perspective regarding cytotoxicity

  • Nicolas Glanzmann
  • Arturene M. L. Carmo
  • Luciana M. R. Antinarelli
  • Elaine S. Coimbra
  • Luiz Antônio S. Costa
  • Adilson D. da Silva
Original Paper
Part of the following topical collections:
  1. XIX - Brazilian Symposium of Theoretical Chemistry (SBQT2017)

Abstract

Ionic liquids (ILs) have been extensively studied and are considered green solvents capable of replacing traditional organic solvents. In this study, seven 1,2,3-triazolium derivative ILs have been synthesized. In order to study the effect of the cation nature on the ILs cytotoxicity, their structures were first identified by 1H, 13C NMR 1D, and 2D spectroscopy. DFT calculations have also been performed in a way to help to provide an insightful structural analysis from 13C NMR spectroscopy. The comparison made with the NMR experimental shifts was quite important to show that the 1,2,3-triazolium derivatives have the expected structure shown here. The in vitro cytotoxicity of ILs toward macrophages showed that among the compounds tested, five did not exhibit expressive cytotoxicity on mammalian cells. Besides the well-established relationship between the carbonic chain size of the cation and the cytotoxicity, the log P of the compounds predicts that the toxicity increases with the size of the carbon chain, demonstrating that the most cytotoxic compound is also the most lipophilic one. The low cytotoxicity effect of ILs on mammalian cells points to their potential application in large-scale by industry.

Graphical abstract

Seven triazolium ILs were synthesized and their in vitro cytotoxicity on murine macrophages showed a relationship with the carbonic chain size.

Keywords

Ionic liquids DFT calculations NMR Lypophilia 

Notes

Acknowledgments

The authors wish to thank FAPEMIG (Process APQ-03830-16 and APQ-02068-14), CNPq, and CAPES for financial support. Also, LASC, ESC, and ADS would like to thank CNPq for the fellowship grant.

Supplementary material

894_2018_3682_MOESM1_ESM.docx (525 kb)
ESM 1 (DOCX 524 kb)

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Departamento de Química, I.C.EUniversidade Federal de Juiz de ForaJuiz de ForaBrazil
  2. 2.Instituto Federal do Sul de MinasMuzambinhoBrazil
  3. 3.Departamento de Parasitologia, Microbiologia e Imunologia, I.C.BUniversidade Federal de Juiz de ForaJuiz de ForaBrazil
  4. 4.NEQC – Núcleo de Estudos em Química Computacional, Departamento de Química, I.C.E.Universidade Federal de Juiz de ForaJuiz de ForaBrazil

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